The development of broadly useful C-P cross-couplings of (hetero)aryl chlorides and HP(O)(R/OR)2 nucleophiles by use of nickel/DalPhos-based catalysts is described, along with findings from DFT studi....

The evolution of palladium-catalyzed C-N and C-O cross-coupling chemistry into first-choice methods for the synthesis of aniline and phenol derivatives can be attributed to innovations in ancillary l...

The first effective base metal-catalyzed protocol for C−O cross-coupling of primary, secondary, and tertiary alcohol-containing N-Boc protected amino alcohols with (hetero)aryl chlorides, affording a....

Employing meso-PAd2-DalPhos (meso-L1) as an ancillary ligand, a single mechanistic landscape provides access to two thermal nickel-catalyzed transformations with broad scope commencing from α-(o-chlor...

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A safe and scalable synthesis of A, a key aryl boronate ester intermediate toward an immunology asset udifitimod, via a Ni-catalyzed Miyaura borylation is reported. High-throughput experimentation, design of experiment, and reagent stability/compatibility studies were used to optimize the reaction conditions and furnish the borylation of aryl sulfamate B in 80–85% yield and >98% purity/potency. Significant hydrogen off-gassing was observed during the reaction, metal remediation, and crystallization steps of the first-generation process, and efforts were made to quantify, understand, and mitigate this off-gassing to ensure a safe and reliable scale-up. Two multikilogram batches of the process were successfully run to afford A in an average 85% yield, >99% potency, and ≤28 ppm residual Ni. Using the mechanistic learnings from this work, a second-generation process was developed which significantly reduced hydrogen off-gassing at all steps of the process, as well as increasing final yield and reducing process mass intensity. This second-generation process was demonstrated on a 1 kg scale to afford the product in 90% yield, >99% purity/potency, and 50 ppm residual Ni.

Focusing on early detection and prevention has skewed awareness of the permanent nature of the disability, a health expert writes.

The asymmetric hydrogenation of substituted naphthalenes with a series of highly enantioenriched oxazoline imino(pyridine) (OIP) molybdenum cyclooctadiene precatalysts is described. The chemoselectivi...

Common belief that Earth-abundant metals are green replacements for palladium may be misleading